EP4378934A1 - Verfahren zur rückgewinnung und herstellung von cyclischem carbonat - Google Patents

Verfahren zur rückgewinnung und herstellung von cyclischem carbonat Download PDF

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Publication number
EP4378934A1
EP4378934A1 EP22849182.5A EP22849182A EP4378934A1 EP 4378934 A1 EP4378934 A1 EP 4378934A1 EP 22849182 A EP22849182 A EP 22849182A EP 4378934 A1 EP4378934 A1 EP 4378934A1
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EP
European Patent Office
Prior art keywords
carbonate
gas
polyalkylene
polyalkylene carbonate
decomposition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22849182.5A
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English (en)
French (fr)
Inventor
Naohisa HAYAMIZU
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Seika Chemicals Co Ltd
Original Assignee
Sumitomo Seika Chemicals Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Seika Chemicals Co Ltd filed Critical Sumitomo Seika Chemicals Co Ltd
Publication of EP4378934A1 publication Critical patent/EP4378934A1/de
Pending legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
    • B01D53/75—Multi-step processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
    • B01D53/81—Solid phase processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C07D317/38—Ethylene carbonate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present disclosure relates to, for example, a recovery method and production method for a cyclic carbonate, which is a decomposition product of polycarbonate.
  • a recovery method and production method for a cyclic carbonate which is a decomposition product of polycarbonate.
  • Ceramic products are widely used in various fields, such as insulating materials, heat-resistant materials, and mechanical parts. These materials are produced by mixing a starting material powder for ceramics with an organic binder, and subjecting the mixture to molding using various methods, such as injection molding, extrusion molding, casting, and tape molding, followed by dewaxing and sintering steps.
  • MLCCs multilayer ceramic capacitors
  • MLCCs are in high demand and are actively produced by this method.
  • organic binder typically, methylcellulose, polyvinyl alcohol, polyvinyl butyral, acrylic resin, and the like have been used. Additionally, as the organic binder, the potentiality of use of a polyalkylene carbonate has also been suggested (e.g., Patent Literature (PTL) 4, PTL 5, and PTL 6).
  • the present inventor has studied whether a polyalkylene carbonate can be effectively used as an organic binder in the production of ceramic components.
  • the present inventor confirmed that the use of a polyalkylene carbonate as an organic binder in the production of ceramics is possible. Furthermore, in the course of the study, the inventor noticed that the gas generated by heating and decomposing a polyalkylene carbonate for dewaxing contains a cyclic carbonate. The generated cyclic carbonate is preferably recovered. Further, cyclic carbonates are highly valuable materials that can be used as a starting material for electrolytes and polycarbonates. Thus, the inventor conducted further study on the recovery of a cyclic carbonate from the polyalkylene carbonate that was used as a binder in the production of ceramics.
  • a method for recovering a cyclic carbonate comprising: (B) recovering a cyclic carbonate contained in a decomposition gas generated by thermal decomposition of a polyalkylene carbonate.
  • cyclic carbonate is at least one member selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, and cyclohexene carbonate.
  • a method for producing a cyclic carbonate comprising: (B) recovering a cyclic carbonate contained in a decomposition gas generated by thermal decomposition of a polyalkylene carbonate.
  • cyclic carbonate is at least one member selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, and cyclohexene carbonate.
  • a method for recovering or producing a cyclic carbonate from a gas obtained by thermally decomposing a polyalkylene carbonate that has been used is provided.
  • Embodiments encompassed by the present disclosure are described in more detail below.
  • the present disclosure encompasses, for example, a method for recovering or producing a cyclic carbonate.
  • the method for recovering or producing a cyclic carbonate encompassed by the present disclosure comprises recovering a cyclic carbonate contained in a decomposition gas generated by thermal decomposition of a polyalkylene carbonate. This method for recovering or producing a cyclic carbonate may be referred to as "the method of the present disclosure.”
  • the polyalkylene carbonate for use in the method of the present disclosure is obtained, for example, by copolymerization of an epoxide and carbon dioxide.
  • epoxides include, but are not limited to, ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, isobutylene oxide, 1-pentene oxide, 2-pentene oxide, 1-hexene oxide, 1-octene oxide, 1-decene oxide, cyclopentene oxide, cyclohexene oxide, styrene oxide, vinylcyclohexane oxide, 3-phenylpropylene oxide, allyl glycidyl ether, methyl glycidyl ether, phenyl glycidyl ether, and epichlorohydrin.
  • ethylene oxide, propylene oxide, 1-butene oxide, and cyclohexene oxide are preferred. These epoxides may be used alone or in a combination of two or more.
  • the obtained polycarbonate contains polyethylene carbonate.
  • the obtained polycarbonate contains propylene oxide, the obtained polycarbonate contains polypropylene carbonate.
  • the epoxide contains 1-butene oxide, the obtained polycarbonate contains polybutylene carbonate.
  • the obtained polycarbonate contains polycyclohexene carbonate.
  • the obtained polycarbonate can be a copolymer.
  • the obtained polycarbonate can be poly(propylene/cyclohexene) carbonate, which is a copolymer.
  • the obtained copolymer may be a random copolymer or a block copolymer. More preferred is a random copolymer.
  • the polyalkylene carbonates may be used alone or in a combination of two or more.
  • the heating temperature for thermal decomposition of polyalkylene carbonate is not limited as long as the temperature is within the range in which a polyalkylene carbonate is decomposed and gasified.
  • the temperature may be 100 to 800°C.
  • the upper limit or the lower limit of the range may be, for example, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, 500, 510, 520, 530, 540, 550, 560, 570, 580, 590, 600, 610, 620, 630, 640, 650, 660, 670, 680, 690, 700, 710, 720, 730, 740, 750,
  • the method of the present disclosure is preferably applicable when a polyalkylene carbonate is used as a binder in the production of ceramic components and is dewaxed by thermal decomposition.
  • the dewaxing step is usually performed in a heating apparatus (e.g., a furnace) while allowing a less-reactive gas, such as nitrogen gas or argon gas, to flow into the apparatus. This is to allow the gas generated by the dewaxing step (heating) to be discharged out of the apparatus.
  • the exhaust gas generated by the dewaxing step becomes a mixed gas of a polyalkylene carbonate decomposition gas and the inflow gas.
  • polyalkylene carbonate decomposition gas when such a gas obtained by thermal decomposition of polyalkylene carbonate contains a small amount of a polyalkylene carbonate decomposition gas (or when the polyalkylene carbonate decomposition gas is diluted), it is preferable to recover the polyalkylene carbonate decomposition gas by first concentrating the polyalkylene carbonate decomposition gas from the obtained gas (the resulting gas).
  • concentration means concentration operations
  • concentration operations include the following (i), (ii), and (iii). These means (i) to (iii) may be used alone or in a combination of two or three.
  • gas adsorbent By bringing the resulting gas into contact with a gas adsorbent, it is possible to (i) cause a polyalkylene carbonate decomposition gas to be adsorbed to a gas adsorbent.
  • gas adsorbent include activated carbon, silica gel, zeolite, and activated alumina.
  • Gas adsorbents may be used alone or in a combination of two or more.
  • the resulting gas can be separated into a polyalkylene carbonate decomposition gas and other gases (e.g., the ambient gases mentioned above) with a gas separation device. That is, it is possible to (ii) separate a polyalkylene carbonate decomposition gas with a gas separation device.
  • the gas separation device include a gas separation membrane and a pressure swing adsorption (PSA) device.
  • a liquid in which a polyalkylene carbonate decomposition gas is concentrated can be obtained. That is, it is possible to (iii) cool and liquefy a polyalkylene carbonate decomposition gas. For example, by performing (iii) above after concentrating the polyalkylene carbonate decomposition gas according to (i) and/or (ii) above, a liquid in which a polyalkylene carbonate decomposition gas is concentrated can be more efficiently obtained.
  • a condensing apparatus can be preferably used for (i) and/or (ii) above, and a cooling apparatus can be preferably used for (iii) above.
  • the cooling temperature is preferably equal to or below the temperature at which the cyclic carbonate contained in the polyalkylene carbonate decomposition gas can be liquefied.
  • the temperature is preferably lower than the boiling point of a cyclic carbonate, which is a decomposition product of polyalkylene carbonate, and is preferably, for example, 5 to 50°C, 5 to 40°C, 5 to 30°C, 10 to 50°C, 10 to 40°C, or 10 to 30°C.
  • the method of the present disclosure enables efficient recovery or production of a cyclic carbonate.
  • the type of the polyalkylene carbonate to be decomposed determines the type of the cyclic carbonate recovered or produced.
  • a polyalkylene carbonate which is obtained by copolymerization of an epoxide and carbon dioxide, produces a cyclic carbonate whose single molecule consists of a single molecule of the epoxide and a single molecule of carbon dioxide.
  • the polyalkylene carbonate for use is a copolymer of ethylene oxide and carbon dioxide
  • ethylene carbonate is produced.
  • propylene carbonate propylene carbonate is produced.
  • it is a copolymer of 1-butene oxide and carbon dioxide butylene carbonate is produced.
  • it is a copolymer of cyclohexene oxide and carbon dioxide cyclohexene carbonate is produced.
  • polyalkylene carbonates may be used alone or in a combination of two or more. If a single type of polyalkylene carbonate is used, a single type of cyclic carbonate is produced. If two or more types of polyalkylene carbonate are used, two or more types of cyclic carbonate are usually produced.
  • the method for recovering or producing a cyclic carbonate described above is preferably applicable, for example, when a polyalkylene carbonate is used as a binder in the production of ceramic components and is dewaxed by thermal decomposition.
  • a polyalkylene carbonate is used, for example, by mixing with an inorganic material, which is a starting material for ceramics.
  • the method of the present disclosure can be preferably performed by heating the mixture and using the obtained polyalkylene carbonate decomposition gas.
  • Polyalkylene carbonates can be preferably used not only for producing ceramics but also as a composition for dispersing an inorganic material. Thus, the scope of application of the method of the present disclosure is not limited to the production of ceramic components.
  • Examples of the inorganic material used in combination with a polyalkylene carbonate include ceramics, conductor powders, glass powders, and phosphor particles, depending on the purpose and use thereof. These may be used alone or in a combination of two or more.
  • Ceramics include aluminum oxide, zirconium oxide, titanium oxide, barium titanate, strontium titanate, zirconium titanate, lead zirconate titanate, lanthanum vanadate, ferrite, zinc oxide, magnesium oxide, beryllium oxide, aluminum nitride, silicon nitride, boron nitride, gallium nitride, silicon carbide, zirconium carbide, magnesium fluoride, tin-doped indium oxide, antimony-doped tin oxide, aluminum-doped zinc oxide, and other ceramics.
  • conductor powders include metals, such as copper, iron, nickel, palladium, platinum, gold, silver, aluminum, tungsten, and tin, alloys thereof, and carbon materials, such as graphite, carbon black, and carbon nanotubes.
  • glass powders include glass powders of various silicon oxides, such as the CaO-Al 2 O 3 -SiO 2 system, MgO-Al 2 O 3 -SiO 2 system, and LiO 2 -Al 2 O 3 -SiO 2 system, bismuth oxide glass, silicate glass, lead glass, zinc glass, and boron glass.
  • silicon oxides such as the CaO-Al 2 O 3 -SiO 2 system, MgO-Al 2 O 3 -SiO 2 system, and LiO 2 -Al 2 O 3 -SiO 2 system
  • bismuth oxide glass such as the CaO-Al 2 O 3 -SiO 2 system, MgO-Al 2 O 3 -SiO 2 system, and LiO 2 -Al 2 O 3 -SiO 2 system
  • bismuth oxide glass such as the CaO-Al 2 O 3 -SiO 2 system, MgO-Al 2 O 3 -SiO 2 system, and
  • Examples of phosphor particles include Y 2 SiO 5 :Ce, CaWO 4 :Pb, BaMgAl 14 O 23 :Eu, Y 2 O 3 :Eu, Y 2 SiO 5 :Eu, Y 3 A 15 O 12 :Eu, Zn 3 (PO 4 ) 2 :Mn, YBO 3 :Eu, GdBO 3 :Eu, ScBO 3 :Eu, LuBO 3 :Eu, Zn 2 SiO 4 :Mn, BaAl 12 O 19 :Mn, CaAl 12 O 19 :Mn, YBO 3 :Tb, BaMgAl 14 O 23 :Mn, LuBO 3 :Tb, and BaMgAl 12 O 23 : Eu.
  • the inorganic material is preferably in a powder form.
  • the size of the inorganic particles is not particularly limited. From the viewpoint of obtaining a dense molded body, it is preferable to use those having a median diameter as determined by a laser diffraction/scattering method of 0.01 to 20 ⁇ m.
  • a polyalkylene carbonate as a binder is thermally decomposed in a dewaxing step etc.
  • thermal decomposition is performed in a nitrogen atmosphere. Since cyclic carbonates decompose into water and carbon dioxide in the presence of oxygen, thermal decomposition is preferably performed in the absence of oxygen to increase the recovery of cyclic carbonate.
  • a cyclic carbonate can be recovered or produced efficiently.
  • the method enables recovery of, as a cyclic carbonate, a significant amount of the polyalkylene carbonate used.
  • the recovery can be made such that the conversion of the polyalkylene carbonate used into a cyclic polycarbonate is 90 mass% or more, more preferably 91, 92, 93, 94, or 95 mass% or more, and still more preferably 96, 97, 98, or 99 mass% or more.
  • a polyalkylene carbonate decomposition gas can be used as a starting material for producing a cyclic carbonate, which is a useful substance; this point is considered to be another advantage of the method of the present disclosure.
  • GC gas chromatograph
  • JHP-5 Japan Analytical Industry Co., Ltd.
  • the gas obtained by decomposing polyalkylene carbonate was confirmed to comprise a cyclic carbonate that is almost 100% derived from the polyalkylene carbonate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
EP22849182.5A 2021-07-26 2022-07-05 Verfahren zur rückgewinnung und herstellung von cyclischem carbonat Pending EP4378934A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021121573 2021-07-26
PCT/JP2022/026754 WO2023008117A1 (ja) 2021-07-26 2022-07-05 環状カーボネートの回収方法及び製造方法

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EP4378934A1 true EP4378934A1 (de) 2024-06-05

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EP (1) EP4378934A1 (de)
JP (1) JPWO2023008117A1 (de)
CN (1) CN117480159A (de)
WO (1) WO2023008117A1 (de)

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JPS558980B2 (de) * 1971-05-13 1980-03-09
JP5787523B2 (ja) * 2008-02-29 2015-09-30 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ １，３−ジオキソラン−２−オンを製造する際の高沸点分離のための膜分離法

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CN117480159A (zh) 2024-01-30
WO2023008117A1 (ja) 2023-02-02

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